YEAR: 1991
Tongues were wagging when Madonna, coming off her Blond Ambition tour and channeling Marilyn Monroe in Harry Winston diamonds and a white ermine stole, walked the red carpet with an equally flashy King of Pop dressed in a beaded jacket and crystal armband. Madge would later abandon her one-date wonder to work the stage and croon "Sooner or Later" from Dick Tracy, which won for Best Song.

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